Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
BODIPY-Based Ratiometric Fluoroionophores with Bidirectional Spectral Shifts for the Selective Recognition of Heavy Metal Ions
Akira HafukaHiroki TaniyamaSang-Hyun SonKoji YamadaMasahiro TakahashiSatoshi OkabeHisashi Satoh
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2013 Volume 86 Issue 1 Pages 37-44


Two novel asymmetric BODIPY fluoroionophores with dipicolylamine (BDP-DPA, dipicolylamine: bis(pyridylmethyl)) and terpyridine (BDP-TPY) are described. These fluoroionophores display opposite wavelength responses on complexation with heavy metal ions. Furthermore, the fluorescence spectra vary depending on the ionic species. In particular, BDP-DPA shows a high affinity toward Cr3+ and upon complexation, the fluorescence spectrum blue-shifts from 591 to 566 nm. In contrast, BDP-TPY preferentially binds to Zn2+ and the fluorescence spectra red-shifts from 539 to 567 nm. BDP-TPY is the first example of asymmetric BODIPY with a pyridyl receptor at the 3 position showing red-shifted fluorescence by complexation with metal ions. The concentration of each metal ion was successfully determined by ratiometric measurement. The wavelength-responses characteristics of these fluoroionophores could be very useful in the development of novel ratiometric fluoroionophores for metal ions.

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© 2013 The Chemical Society of Japan
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